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| United States Patent | 5,332,833 |
| Sekiya , et al. | July 26, 1994 |
The .beta.-oxo-.beta.-benzenepropanethioamide derivative of the present invention has potassium channel opening action and is useful for treatment of hypertension, asthma, hypersensitive colon syndrome, and enteritis through pharmacological actions including blood vessel dilation, bronchial tract dilation, relaxation of gastrointestinal tract smooth muscle, and the like. The present invention also includes a pharmaceutical composition containing, as the active ingredient, the compound of the present invention and a method for producing the same.
| Inventors: | Sekiya; Tetsuo (Kanagawa, JP); Tsutsui; Mikio (Kanagawa, JP); Shimpuku; Tetsuro (Tokyo, JP); Nagano; Tatsuo (Tokyo, JP); Hayashi; Junko (Tokyo, JP); Seino; Asami (Kanagawa, JP) |
| Assignee: | Mitsubishi Kasei Corporation (Tokyo, JP) |
| Appl. No.: | 996404 |
| Filed: | December 23, 1992 |
| Dec 26, 1991[JP] | 3-345657 |
| Current U.S. Class: | 548/338.5; 544/324; 544/335; 544/374; 546/293; 546/331; 548/205; 548/235; 548/267.8; 548/325.5; 548/559; 564/74; 564/78 |
| Intern'l Class: | C07C 327/38; C07C 327/48; C07D 233/96; A61K 031/165 |
| Field of Search: | 548/338.5,325.5,267.8,205,235,559 564/74,78 514/599,247,269,357,365,374,383,399,427 546/293,331 544/335,374,324 |
| 4028409 | Jun., 1977 | Kramer et al. | 564/74. |
| 4252819 | Feb., 1981 | Hirata et al. | 548/338. |
| 4299845 | Nov., 1981 | Loebenberg et al. | 514/599. |
| 5185375 | Feb., 1993 | Cook et al. | 564/74. |
| Foreign Patent Documents | |||
| 0306440 | Mar., 1989 | EP. | |
| 2183639 | Jun., 1987 | GB | 564/74. |
Darre et al., Bulletin De La Societe Chimique De France No. 3-4 1975, pp. 829-834. Barluenga et al., J. Chem. Soc. Perkins Trans. 1 1988 pp. 1739-1744. Datta et al., Synthesis, No. 7 1988 pp. 556-557. Okujima et al., Chemical Abstracts, vol. 116, 1992, p. 786 Abstract No. 83371j Abstracting JP 03 232853. Yates et al., Tetrahedron, vol. 44, No. 11, pp. 3159-3170 (1988). |
TABLE 1
__________________________________________________________________________
Com-
pound
No. R.sup.1
R.sup.2
R.sup.3
R.sup.4
X.sup.1 X.sup.2 X.sup.3
__________________________________________________________________________
1 H H H methyl
H H H
2 H H H methyl
2-(1-imidazolyl)
H H
3 H H H methyl
3-(1-imidazolyl)
H H
4 H H H methyl
4-(1-imidazolyl)
H H
5 H H H methyl
4-fluoro H H
6 H H --CH.sub.2 CH.sub.2 CH.sub.2 --
4-(1-imidazolyl)
H H
7 H H --CH.sub.2 CH.sub.2 CH.sub.2 --
4-(2-methyl-1-imidazolyl)
H H
8 H H --CH.sub.2 CH.sub.2 CH.sub.2 --
4-(2-ethyl-1-imidazolyl)
H H
9 H H --CH.sub.2 CH.sub.2 CH.sub.2 --
4-(2-isopropyl-1-imidazolyl)
H H
10 H H --CH.sub.2 CH.sub.2 CH.sub.2 --
4-(2-propyl-1-imidazolyl)
H H
11 H H --CH.sub.2 CH.sub.2 CH.sub.2 --
4(2-phenyl-1-imidazolyl)
H H
12
H H --CH.sub.2 CH.sub.2 CH.sub.2 --
4-(2-iodo-1-imidazolyl)
H H
13 H H --CH.sub.2 CH.sub.2 CH.sub.2 --
4-(2-methoxy-1-imidazolyl)
H H
14 H H --CH.sub.2 CH.sub.2 CH.sub.2 --
4-(2-methylthio-1-imidazolyl)
H H
15 H H --CH.sub.2 CH.sub.2 CH.sub.2 --
4-(2-cyano-1-imidazolyl)
H H
16 H H --CH.sub.2 CH.sub.2 CH.sub.2 --
4-(2-chloro-1-imidazolyl)
H H
17 H H --CH.sub.2 CH.sub.2 CH.sub.2 --
4-(4-methyl-1-imidazolyl)
H H
18 H H --CH.sub.2 CH.sub.2 CH.sub.2 --
4-(4-methyl-1-imidazolyl)
H H
19 H H --CH.sub.2 CH.sub.2 CH.sub.2 --
4-(5-methyl-1-imidazolyl)
H H
20 H H --CH.sub.2 CH.sub.2 CH.sub.2 --
4-(2-fluoromethyl-1-imidazolyl)
H H
21 H H --CH.sub.2 CH.sub.2 CH.sub.2 --
4-(2-difluoromethyl-1-imidazolyl)
H H
22 H H --CH.sub.2 CH.sub.2 CH.sub.2 --
4-(2-trifluoromethyl-1-imidazolyl)
H H
23 H H --CH.sub.2 CH.sub.2 CH.sub.2 --
4-(4,5-dichloro-1-imidazolyl)
H H
24 H H --CH.sub.2 CH.sub.2 CH.sub.2 --
4-(1-imidazolyl)
3-fluoro H
25 H H --CH.sub.2 CH.sub.2 CH.sub.2 --
4-(1-imidazolyl)
3-chloro H
26 H H --CH.sub.2 CH.sub.2 CH.sub.2 --
4-(1-imidazolyl)
3-bromo H
27 H H --CH.sub.2 CH.sub.2 CH.sub.2 --
4-(1-imidazolyl)
3-iodo H
28 H H --CH.sub.2 CH.sub.2 CH.sub.2 --
4-(1-imidazolyl)
3-cyano H
29 H H --CH.sub.2 CH.sub.2 CH.sub.2 --
4-(1-imidazolyl)
3-methyl H
30 H H --CH.sub.2 CH.sub.2 CH.sub.2 --
4-(1-imidazolyl)
3-ethyl H
31 H H --CH.sub.2 CH.sub.2 CH.sub.2 --
4-(1-imidazolyl)
3-isopropyl
H
32 H H --CH.sub.2 CH.sub.2 CH.sub.2 --
4-(1-imidazolyl)
3-propyl H
33 H H --CH.sub.2 CH.sub.2 CH.sub.2 --
4-(1-imidazolyl)
3-methoxy
H
34 H H --CH.sub.2 CH.sub.2 CH.sub.2 --
4-(1-imidazolyl)
3-ethoxy H
35 H H --CH.sub.2 CH.sub.2 CH.sub.2 --
4-(1-imidazolyl)
3-isopropoxy
H
36 H H --CH.sub.2 CH.sub.2 CH.sub.2 --
4-(1-imidazolyl)
3-propoxy
H
37
H H --CH.sub.2 CH.sub.2 CH.sub.2 --
4-(1-imidazolyl)
3-trifluoromethyl
H
38 H H --CH.sub.2 CH.sub.2 CH.sub.2 --
3-(1-imidazolyl)
H H
39 H H --CH.sub.2 CH.sub.2 CH.sub.2 --
3-(2-methyl-1-imidazolyl)
H H
40 H H --CH.sub.2 CH.sub.2 CH.sub.2 --
3-(2-ethyl-1-imidazolyl)
H H
41 H H --CH.sub.2 CH.sub.2 CH.sub.2 --
3-(2-isopropyl-1-imidazolyl)
H H
42 H H --CH.sub.2 CH.sub.2 CH.sub.2 --
3-(2-propyl-1-imidazolyl)
H H
43 H H --CH.sub.2 CH.sub.2 CH.sub.2 --
3-(2-phenyl-1-imidazolyl)
H H
44 H H --CH.sub.2 CH.sub.2 CH.sub.2 --
3-(2-iodo-1-imidazolyl)
H H
45 H H --CH.sub.2 CH.sub.2 CH.sub.2 --
3-(2-methoxy-1-imidazolyl)
H H
46 H H --CH.sub.2 CH.sub.2 CH.sub.2 --
3-(2-methylthio-1-imidazolyl)
H H
47 H H --CH.sub.2 CH.sub.2 CH.sub.2 --
3-(2-cyano-1-imidazolyl)
H H
48 H H --CH.sub.2 CH.sub.2 CH.sub.2 --
3-(2-chloro-1-imidazolyl)
H H
49 H H --CH.sub.2 CH.sub.2 CH.sub.2 --
3-(2-methyl-1-imidazolyl)
H H
50 H H --CH.sub.2 CH.sub.2 CH.sub.2 --
3-(4-methyl-1-imidazolyl)
H H
51 H H --CH.sub.2 CH.sub.2 CH.sub.2 --
3-(5-methyl-1-imidazolyl)
H H
52 H H --CH.sub.2 CH.sub.2 CH.sub.2 --
3-(2-fluoromethyl-1-imidazolyl)
H H
53 H H --CH.sub.2 CH.sub.2 CH.sub.2 --
3-(2-difluoromethyl-1-imidazolyl)
H H
54 H H --CH.sub.2 CH.sub.2 CH.sub.2 --
3-(2-trifluoromethyl-1-imidazolyl)
H H
55 H H --CH.sub.2 CH.sub.2 CH.sub.2 --
3-(4,5-dichloro-1-imidazolyl)
H H
56 H H --CH.sub.2 CH.sub.2 CH.sub.2 --
3-(1-imidazolyl)
4-fluoro H
57 H H --CH.sub.2 CH.sub.2 CH.sub.2 --
3-(1-imidazolyl)
4-chloro H
58 H H --CH.sub.2 CH.sub.2 CH.sub.2 --
3-(1-imidazolyl)
4-bromo H
59 H H --CH.sub.2 CH.sub.2 CH.sub.2 --
3-(1-imidazolyl)
4-iodo H
60 H H --CH.sub.2 CH.sub.2 CH.sub.2 --
3-(1-imidazolyl)
4-cyano H
61 H H --CH.sub.2 CH.sub.2 CH.sub.2 --
3-(1-imidazolyl)
4-methyl H
62
H H --CH.sub.2 CH.sub.2 CH.sub.2 --
3-(1-imidazolyl)
4-ethyl H
63 H H --CH.sub.2 CH.sub.2 CH.sub.2 --
3-(1-imidazolyl)
4-isopropyl
H
64 H H --CH.sub.2 CH.sub.2 CH.sub.2 --
3-(1-imidazolyl)
4-propyl H
65 H H --CH.sub.2 CH.sub.2 CH.sub.2 --
3-(1-imidazolyl)
4-methoxy
H
66 H H --CH.sub.2 CH.sub.2 CH.sub.2 --
3-(1-imidazolyl)
4-ethoxy H
67 H H --CH.sub.2 CH.sub.2 CH.sub.2 --
3-(1-imidazolyl)
4-isopropoxy
H
68 H H --CH.sub.2 CH.sub.2 CH.sub.2 --
3-(1-imidazolyl)
4-propoxy
H
69 H H --CH.sub.2 CH.sub.2 CH.sub.2 --
3-(1-imidazolyl)
4-trifluoromethyl
H
70 H H --CH.sub.2 CH.sub.2 CH.sub.2 --
3-(1-imidazolyl)
H H
71 H H --CH.sub.2 CH.sub.2 CH.sub.2 --
3-(2-methoxy-1-imidazolyl)
H H
72 H H --CH.sub.2 CH.sub.2 CH.sub.2 --
3-(2-methylthio-1-imidazolyl)
H H
73 H H --CH.sub.2 CH.sub.2 CH.sub.2 --
2-(1-imidazolyl)
H H
74 H H --CH.sub.2 CH.sub.2 CH.sub.2 --
2-(2-methyl-1-imidazolyl)
H H
75 H H --CH.sub.2 CH.sub.2 CH.sub.2 --
2-(2-ethyl-1-imidazolyl)
H H
76 H H --CH.sub.2 CH.sub.2 CH.sub.2 --
2-(2-isopropyl-1-imidazolyl)
H H
77 H H --CH.sub.2 CH.sub.2 CH.sub.2 --
2-(2-propyl-1-imidazolyl)
H H
78 H H --CH.sub.2 CH.sub.2 CH.sub.2 --
2-(2-phenyl-1-imidazolyl)
H H
79 H H --CH.sub.2 CH.sub.2 CH.sub.2 --
2-(2-iodo-1-imidazolyl)
H H
80 H H --CH.sub.2 CH.sub.2 CH.sub.2 --
2-(2-methoxy-1-imidazolyl)
H H
81 H H --CH.sub.2 CH.sub.2 CH.sub.2 --
2-(2-methylthio-1-imidazolyl)
H H
82 H H --CH.sub.2 CH.sub.2 CH.sub.2 --
2-(2-cyano-1-imidazolyl)
H H
83 H H --CH.sub.2 CH.sub.2 CH.sub.2 --
2-(2-chloro-1-imidazolyl)
H H
84 H H --CH.sub.2 CH.sub.2 CH.sub.2 --
2-(2-metyl-1-imidazolyl)
H H
85 H H --CH.sub.2 CH.sub.2 CH.sub.2 --
2-(4-metyl-1-imidazolyl)
H H
86 H H --CH.sub.2 CH.sub.2 CH.sub.2 --
2-(5-metyl-1-imidazolyl)
H H
87
H H --CH.sub.2 CH.sub.2 CH.sub.2 --
2-(2-fluoromethyl-1-imidazolyl)
H H
88 H H --CH.sub.2 CH.sub.2 CH.sub.2 --
2-(2-difluoromethyl-1-imidazolyl)
H H
89 H H --CH.sub.2 CH.sub.2 CH.sub.2 --
2-(2-trifluoromethyl-1-imidazolyl)
H H
90 H H --CH.sub.2 CH.sub.2 CH.sub.2 --
2-(4,5-dichloro-1-imidazolyl)
H H
91 H H --CH.sub.2 CH.sub.2 CH.sub.2 --
2-(1-imidazolyl)
3-fluoro H
92 H H --CH.sub.2 CH.sub.2 CH.sub.2 --
2-(1-imidazolyl)
3-chloro H
93 H H --CH.sub.2 CH.sub.2 CH.sub.2 --
2-(1-imidazolyl)
3-bromo H
94 H H --CH.sub.2 CH.sub.2 CH.sub.2 --
2-(1-imidazolyl)
3-iodo H
95 H H --CH.sub.2 CH.sub.2 CH.sub.2 --
2-(1-imidazolyl)
3-cyano H
96 H H --CH.sub.2 CH.sub.2 CH.sub.2 --
2-(1-imidazolyl)
3-methyl H
97 H H --CH.sub.2 CH.sub.2 CH.sub.2 --
2-(1-imidazolyl)
3-ethyl H
98 H H --CH.sub.2 CH.sub.2 CH.sub.2 --
2-(1-imidazolyl)
3-isopropyl
H
99 H H --CH.sub.2 CH.sub.2 CH.sub.2 --
2-(1-imidazolyl)
3-propyl H
100 H H --CH.sub.2 CH.sub.2 CH.sub.2 --
2-(1-imidazolyl)
3-methoxy
H
101 H H --CH.sub.2 CH.sub.2 CH.sub.2 --
2-(1-imidazolyl)
3-ethoxy H
102 H H --CH.sub.2 CH.sub.2 CH.sub.2 --
2-(1-imidazolyl)
3-isopropoxy
H
103 H H --CH.sub.2 CH.sub.2 CH.sub.2 --
2-(1-imidazolyl)
3-propoxy
H
104 H H --CH.sub.2 CH.sub.2 CH.sub.2 --
2-(1-imidazolyl)
3-trifluoromethyl
H
105 H H methyl
methyl
H H H
106 H H methyl
methyl
4-(1-imidazolyl)
H H
107 H H methyl
methyl
4-(2-methyl-1-imidazolyl)
H H
108 H H methyl
methyl
4-(2-ethyl-1-imidazolyl)
H H
109 H H methyl
methyl
4-(2-isopropyl-1-imidazolyl)
H H
110 H H methyl
methyl
4-(2-propyl-1-imidazolyl)
H H
111 H H methyl
methyl
4-(2-phenyl-1-imidazolyl)
H H
112 H H methyl
methyl
4-(2-iodo-1-imidazolyl)
H H
113 H H methyl
methyl
4-(2-methoxy-1-imidazolyl)
H H
114 H H methyl
methyl
4-(2-methylthio-1-imidazolyl)
H H
115 H H methyl
methyl
4-(2-cyano-1-imidazolyl)
H H
116 H H methyl
methyl
4-(2-chloro-1-imidazolyl)
H H
117 H H methyl
methyl
4-(2-methyl-1-imidazolyl)
H H
118 H H methyl
methyl
4-(4-methyl-1-imidazolyl)
H H
119 H H methyl
methyl
4-(5-methyl-1-imidazolyl)
H H
120 H H methyl
methyl
4-(2-fluoromethyl-1-imidazolyl)
H H
121 H H methyl
methyl
4-(2-difluoromethyl-1-imidazolyl)
H H
122 H H methyl
methyl
4-(2-trifluoromethyl-1-imidazolyl)
H H
123 H H methyl
methyl
4-(4,5-dichloro-1-imidazolyl)
H H
124 H H methyl
methyl
4-(1-imidazolyl)
3-fluoro H
125 H H methyl
methyl
4-(1-imidazolyl)
3-chloro H
126 H H methyl
methyl
4-(1-imidazolyl)
3-bromo H
127 H H methyl
methyl
4-(1-imidazolyl)
3-iodo H
128 H H methyl
methyl
4-(1-imidazolyl)
3-cyano H
129 H H methyl
methyl
4-(1-imidazolyl)
3-methy H
130 H H methyl
methyl
4-(1-imidazolyl)
3-ethyl H
131 H H methyl
methyl
4-(1-imidazolyl)
3-isopropyl
H
132 H H methyl
methyl
4-(1-imidazolyl)
3-propyl H
133 H H methyl
methyl
4-(1-imidazolyl)
3-methoxy
H
134 H H methyl
methyl
4-(1-imidazolyl)
3-ethoxy H
135 H H methyl
methyl
4-(1-imidazolyl)
3-isopropoxy
H
136 H H methyl
methyl
4-(1-imidazolyl)
3-propoxy
H
137 H H methyl
methyl
4-(1-imidazolyl)
3-trifluoromethyl
H
138 H H methyl
methyl
3-(1-imidazolyl)
H H
139 H H methyl
methyl
3-(2-methyl-1-imidazolyl)
H H
140 H H methyl
methyl
3-(2-ethyl-1-imidazolyl)
H H
141 H H methyl
methyl
3-(2-isopropyl-1-imidazolyl)
H H
142 H H methyl
methyl
3-(2-propyl-1-imidazolyl)
H H
143 H H methyl
methyl
3-(2-phenyl-1-imidazolyl)
H H
144 H H methyl
methyl
3-(2-iodo-1-imidazolyl)
H H
145 H H methyl
methyl
3-(2-methoxy-1-imidazolyl)
H H
146 H H methyl
methyl
3-(2-methylthio-1-imidazolyl)
H H
147 H H methyl
methyl
3-(2-cyano-1-imidazolyl)
H H
148 H H methyl
methyl
3-(2-chloro-1-imidazolyl)
H H
149 H H methyl
methyl
3-(2-methyl-1-imidazolyl)
H H
150 H H methyl
methyl
3-(4-methyl-1-imidazolyl)
H H
151 H H methyl
methyl
3-(5-methyl-1-imidazolyl)
H H
152 H H methyl
methyl
3-(2-fluoromethyl-1-imidazolyl)
H H
153 H H methyl
methyl
3-(2-difluoromethyl-1-imidazolyl)
H H
154 H H methyl
methyl
3-(2-trifluoromethyl-1-imidazolyl)
H H
155 H H methyl
methyl
3-(4,5-dichloro-1-imidazolyl)
H H
156 H H methyl
methyl
3-(1-imidazolyl)
4-fluoro H
157 H H methyl
methyl
3-(1-imidazolyl)
4-chloro H
158 H H methyl
methyl
3-(1-imidazolyl)
4-bromo H
159 H H methyl
methyl
3-(1-imidazolyl)
4-iodo H
160 H H methyl
methyl
3-(1-imidazolyl)
4-cyano H
161 H H methyl
methyl
3-(1-imidazolyl)
4-methyl H
162 H H methyl
methyl
3-(1-imidazolyl)
4-ethyl H
163 H H methyl
methyl
3-(1-imidazolyl)
4-isopropyl
H
164 H H methyl
methyl
3-(1-imidazolyl)
4-propyl H
165 H H methyl
methyl
3-(1-imidazolyl)
4-methoxy
H
166 H H methyl
methyl
3-(1-imidazolyl)
4-ethoxy H
167 H H methyl
methyl
3-(1-imidazolyl)
4-isopropoxy
H
168 H H methyl
methyl
3-(1-imidazolyl)
4-propoxy
H
169 H H methyl
methyl
3-(1-imidazolyl)
4-trifluoromethyl
H
170 H H methyl
methyl
3-(1-imidazolyl)
H H
171 H H methyl
methyl
3-(2-methoxy-1-imidazoly)
H H
172 H H methyl
methyl
3-(2-methythio-1-imidazolyl)
H H
173 H H methyl
methyl
2-(1-imidazolyl)
H H
174 H H methyl
methyl
2-(2-methyl-1-imidazolyl)
H H
175 H H methyl
methyl
2-(2-ethyl-1-imidazolyl)
H H
176 H H methyl
methyl
2-(2-isopropyl-1-imidazolyl)
H H
177 H H methyl
methyl
2-(2-propyl-1-imidazolyl)
H H
178 H H methyl
methyl
2-(2-phenyl-1-imidazolyl)
H H
179 H H methyl
methyl
2-(2-iodo-1-imidazolyl)
H H
180 H H methyl
methyl
2-(2-methoxy-1-imidazolyl)
H H
181 H H methyl
methyl
2-(2-methylthio-1-imidazolyl)
H H
182 H H methyl
methyl
2-(2-cyano-1-imidazolyl)
H H
183 H H methyl
methyl
2-(2-chloro-1-imidazolyl)
H H
184 H H methyl
methyl
2-(2-methyl-1-imidazolyl)
H H
185 H H methyl
methyl
2-(4-methyl-1-imidazolyl)
H H
186 H H methyl
methyl
2-(5-methyl-1-imidazolyl)
H H
187 H H methyl
methyl
2-(2-fluoromethyl-1-imidazolyl)
H H
188 H H methyl
methyl
2-(2-difluoromethyl-1-imidazolyl)
H H
189 H H methyl
methyl
2-(2-trifluoromethyl-1-imidazolyl)
H H
190 H H methyl
methyl
2-(4,5-dichloro-1-imidazolyl)
H H
191 H H methyl
methyl
2-(1-imidazolyl)
3-fluoro H
192 H H methyl
methyl
2-(1-imidazolyl)
3-chloro H
193 H H methyl
methyl
2-(1-imidazolyl)
3-bromo H
194 H H methyl
methyl
2-(1-imidazolyl)
3-iodo H
195 H H methyl
methyl
2-(1-imidazolyl)
3-cyano H
196 H H methyl
methyl
2-(1-imidazolyl)
3-methyl H
197 H H methyl
methyl
2-(1-imidazolyl)
3-ethyl H
198 H H methyl
methyl
2-(1-imidazolyl)
3-isopropyl
H
199 H H methyl
methyl
2-(1-imidazolyl)
3-propyl H
200 H H methyl
methyl
2-(1-imidazolyl)
3-methoxy
H
201 H H methyl
methyl
2-(1-imidazolyl)
3-ethoxy H
202 H H methyl
methyl
2-(1-imidazolyl)
3-isopropoxy
H
203 H H methyl
methyl
2-(1-imidazolyl)
3-propoxy
H
204 H H methyl
methyl
2-(1-imidazolyl)
3-trifluoromethyl
H
205 H H methyl
methyl
4-cyano H H
206 H H methyl
methyl
4-chloro H H
207 H methyl H H H H H
208 H methyl H H 4-fluoro H H
209 H methyl H H 4-methoxy H H
210 H methyl H H 2-(1-imidazolyl)
H H
211 H methyl H H 3-(1-imidazolyl)
H H
212 H methyl H H 4-(1-imidazolyl)
H H
213 H methyl H H 4-(1-imidazolyl)
3-chloro H
214 H methyl H ethyl
4-(1-imidazolyl)
H H
215 H methyl H isopropyl
4-(1-imidazolyl)
H H
216 H methyl H propyl
4-(1-imidazolyl)
H H
217 H methyl H hexyl
H H H
218 H methyl methyl
methyl
4-methyl H H
219 H methyl methyl
methyl
4-methoxy H H
220 H methyl methyl
methyl
4-dimethylamino H H
221 H methyl methyl
methyl
4-fluoro H H
222 H methyl methyl
methyl
4-bromo H H
223 H methyl methyl
methyl
4-chloro H H
224 H methyl methyl
methyl
4-cyano H H
225 H methyl methyl
methyl
4-trifluoromethy
H H
226 H methyl methyl
methyl
4-(1-imidazolyl)
H H
227 H methyl methyl
methyl
4-(2-methyl-1-imidazolyl)
H H
228 H methyl methyl
methyl
4-(2-ethyl-1-imidazolyl)
H H
229 H methyl methyl
methyl
4-(2-isopropyl-1-imidazolyl)
H H
230 H methyl methyl
methyl
4-(2-propyl-1-imidazolyl)
H H
231 H methyl methyl
methyl
4-(2-phenyl-1-imidazolyl)
H H
232 H methyl methyl
methyl
4-(2-iodo-1-imidazolyl)
H H
233 H methyl methyl
methyl
4-(2-methoxyl-1-imidazolyl)
H H
234 H methyl methyl
methyl
4-(2-methylthio-1-imidazolyl)
H H
235 H methyl methyl
methyl
4-(2-cyano-1-imidazolyl)
H H
236 H methyl methyl
methyl
4-(2-chloro-1-imidazolyl)
H H
237 H methyl methyl
methyl
4-(2-methyl-1-imidazolyl)
H H
238 H methyl methyl
methyl
4-(4-methyl-1-imidazolyl)
H H
239 H methyl methyl
methyl
4-(5-methyl-1-imidazolyl)
H H
240 H methyl methyl
methyl
4-(2-fluoromethyl-1-imidazolyl)
H H
241 H methyl methyl
methyl
4-(2-difluoromethyl-1-imidazolyl)
H H
242 H methyl methyl
methyl
4-(2-trimethyl-1-imidazolyl)
H H
243 H methyl methyl
methyl
4-(4,5-dichloro-1-imidazolyl)
H H
244 H methyl methyl
methyl
4-(1-imidazolyl)
3-fluoro H
245 H methyl methyl
methyl
4-(1-imidazolyl)
3-chloro H
246 H methyl methyl
methyl
4-(1-imidazolyl)
3-bromo H
247 H methyl methyl
methyl
4-(1-imidazolyl)
3-iodo H
248 H methyl methyl
methyl
4-(1-imidazolyl)
3-cyano H
249 H methyl methyl
methyl
4-(1-imidazolyl)
3-methyl H
250 H methyl methyl
methyl
4-(1-imidazolyl)
3-ethyl H
251 H methyl methyl
methyl
4-(1-imidazolyl)
3-isopropyl
H
252 H methyl methyl
methyl
4-(1-imidazolyl)
3-propyl H
253 H methyl methyl
methyl
4-(1-imidazolyl)
3-methoxy
H
254 H methyl methyl
methyl
4-(1-imidazolyl)
3-ethoxy H
255 H methyl methyl
methyl
4-(1-imidazolyl)
3-isopropoxy
H
256 H methyl methyl
methyl
4-(1-imidazolyl)
3-propoxy
H
257 H methyl methyl
methyl
4-(1-imidazolyl)
3-trifluoromethyl
H
258 H methyl methyl
methyl
4-(2-pyridyl) H H
259 H methyl methyl
methyl
4-(4-pyridyl) H H
260 H methyl methyl
methyl
4-(3-pyridyl) H H
261 H methyl methyl
methyl
3-fluoro H H
262 H methyl methyl
methyl
3-chloro H H
263 H methyl methyl
methyl
3-methyl H H
264 H methyl methyl
methyl
3-methoxy H H
265 H methyl methyl
methyl
3-(1-imidazolyl)
H H
266 H methyl methyl
methyl
3-(2-ethyl-1-imidazolyl)
H H
267 H methyl methyl
methyl
3-(2-isopropyl-1-imidazolyl)
H H
268 H methyl methyl
methyl
3-(2-propyl-1-imidazolyl)
H
269 H methyl methyl
methyl
3-(2-phenyl-1-imidazolyl)
H H
270 H methyl methyl
methyl
3-(2-iodo-1-imidazolyl)
H H
271 H methyl methyl
methyl
3-(2-methoxyy-1-imidazolyl)
H H
272 H methyl methyl
methyl
3-(2-methylthio-1-imidazolyl)
H H
273 H methyl methyl
methyl
3-(2-cyano-1-imidazolyl)
H H
274 H methyl methyl
methyl
3-(2-chloro-1-imidazolyl)
H H
275 H methyl methyl
methyl
3-(2-methyl-1-imidazolyl)
H H
276 H methyl methyl
methyl
3-(4-methyl-1-imidazolyl)
H H
277 H methyl methyl
methyl
3-(5-methyl-1-imidazolyl)
H H
278 H methyl methyl
methyl
3-(2-fluoromethyl-1-imidazolyl)
H H
279 H methyl methyl
methyl
3-(2-difluoromethyl-1-imidazolyl)
H H
280 H methyl methyl
methyl
3-(2-trifluoromethyl-1-imidazolyl)
H H
281 H methyl methyl
methyl
3-(4,5-dichloro-1-imidazolyl)
H H
282 H methyl methyl
methyl
3-(1-imidazolyl)
4-fluoro H
283 H methyl methyl
methyl
3-(1-imidazolyl)
4-chloro H
284 H methyl methyl
methyl
3-(1-imidazolyl)
4-bromo H
285 H methyl methyl
methyl
3-(1-imidazolyl)
4-iodo H
286 H methyl methyl
methyl
3-(1-imidazolyl)
4-cyano H
287 H methyl methyl
methyl
3-(1-imidazolyl)
4-methyl H
288 H methyl methyl
methyl
3-(1-imidazolyl)
4-ethyl H
289 H methyl methyl
methyl
3-(1-imidazolyl)
4-isopropyl
H
290 H methyl methyl
methyl
3-(1-imidazolyl)
4-propyl H
291 H methyl methyl
methyl
3-(1-imidazolyl)
4-methoxy
H
292 H methyl methyl
methyl
3-(1-imidazolyl)
4-ethoxy H
293 H methyl methyl
methyl
3-(1-imidazolyl)
4-isopropoxy
H
294 H methyl methyl
methyl
3-(1-imidazolyl)
4-propoxy
H
295 H methyl methyl
methyl
3-(1-imidazolyl)
4-trifluoromethyl
H
296 H methyl methyl
methyl
3-(1-imidazolyl)
H H
297 H methyl methyl
methyl
3-(2-methoxy-1-imidazolyl)
H H
298 H methyl methyl
methyl
3-(2-methylthio-1-imidazolyl)
H H
299 H methyl methyl
methyl
3-(2-pyridyl) H H
300 H methyl methyl
methyl
3-(3-pyridyl) H H
301 H methyl methyl
methyl
3-(4-pyridyl) H H
302 H methyl methyl
methyl
2-(1-imidazolyl)
H H
303 H methyl methyl
methyl
2-(2-methyl-1-imidazolyl)
H H
304 H methyl methyl
methyl
2-(2-ethyl-1-imidazolyl)
H H
305 H methyl methyl
methyl
2-(2-isopropyl-1-imidazolyl)
H H
306 H methyl methyl
methyl
2-(2-propyl-1-imidazolyl)
H H
307 H methyl methyl
methyl
2-(2-phenyl-1-imidazolyl)
H H
308 H methyl methyl
methyl
2-(2-iodo-1-imidazolyl)
H H
309 H methyl methyl
methyl
2-(2-methoxy-1-imidazolyl)
H H
310 H methyl methyl
methyl
2-(2-methylthio-1-imidazolyl)
H H
311 H methyl methyl
methyl
2-(2-cyano-1-imidazolyl)
H H
312 H methyl methyl
methyl
2-(2-chloro-1-imidazolyl)
H H
313 H methyl methyl
methyl
2-(2-methyl-1-imidazolyl)
H H
314 H methyl methyl
methyl
2-(4-methyl-1-imidazolyl)
H H
315 H methyl methyl
methyl
2-(5-methyl-1-imidazolyl)
H H
316 H methyl methyl
methyl
2-(2-fluoromethyl-1-imidazolyl)
H H
317 H methyl methyl
methyl
2-(2-difluoromethyl-1-imidazolyl)
H H
318 H methyl methyl
methyl
2-(2-trifluoromethyl-1-imidazolyl)
H H
319 H methyl methyl
methyl
2-(4,5-dichloro-1-imidazolyl)
H H
320 H methyl methyl
methyl
2-(1-imidazolyl)
3-fluoro H
321 H methyl methyl
methyl
2-(1-imidazolyl)
3-chloro H
322 H methyl methyl
methyl
2-(1-imidazolyl)
3-bromo H
323 H methyl methyl
methyl
2-(1-imidazolyl)
3-iodo H
324 H methyl methyl
methyl
2-(1-imidazolyl)
3-cyano H
325 H methyl methyl
methyl
2-(1-imidazolyl)
3-methyl H
326 H methyl methyl
methyl
2-(1-imidazolyl)
3-ethyl H
327 H methyl methyl
methyl
2-(1-imidazolyl)
3-isopropyl
H
328 H methyl methyl
methyl
2-(1-imidazolyl)
3-propyl H
329 H methyl methyl
methyl
2-(1-imidazolyl)
3-methoxy
H
330 H methyl methyl
methyl
2-(1-imidazolyl)
3-ethoxy H
331 H methyl methyl
methyl
2-(1-imidazolyl)
3-isopropoxy
H
332 H methyl methyl
methyl
2-(1-imidazolyl)
3-propoxy
H
333 H methyl methyl
methyl
2-(1-imidazolyl)
3-trifluoromethyl
H
334 H methyl methyl
methyl
3-(2-pyridyl) H H
335 H methyl methyl
methyl
3-(3-pyridyl) H H
336 H methyl methyl
methyl
3-(4-pyridyl) H H
337 H methyl methyl
methyl
3-methoxy 4-methoxy
5-methoxy
338 H methyl ethyl
ethyl
4-(1-imidazolyl)
H H
339 H methyl ethyl
ethyl
4-(1-imidazolyl)
3-fluoro H
340 H methyl hexyl
hexyl
4-(1-imidazolyl)
H H
341 H methyl methyl
hexyl
4-(1-imidazolyl)
H H
342 H methyl --CH.sub.2 CH.sub.2 --
4-(1-imidazolyl)
H H
343 H methyl --CH.sub.2 CH.sub.2 --
3-(1-imidazolyl)
H H
344 H methyl --CH.sub.2 CH.sub.2 --
2-(1-imidazolyl)
H H
345 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
H H H
346 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
4-fluoro H H
347 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
4-chloro H H
348 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
4-bromo H H
349 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
4-iodo H H
350 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
4-methyl H H
351 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
4-methoxy H H
352 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
4-trifluoromethyl
H H
353 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
4-cyano H H
354 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
4-nitro H H
355 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
4-dimethylamino H H
356 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
4-(1-imidazolyl)
H H
357 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
4-(2-methyl-1-imidazolyl)
H H
358 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
4-(2-ethyl-1-imidazolyl)
H H
359 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
4-(2-isopropyl-1-imidazolyl)
H H
360 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
4-(2-propyl-1-imidazolyl)
H H
361 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
4-(2-phenyl-1-imidazolyl)
H H
362 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
4-(2-iodo-1-imidazolyl)
H H
363 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
4-(2-methoxy-1-imidazolyl)
H H
364 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
4-(2-methylthio-1-imidazolyl)
H H
365 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
4-(2-cyano-1-imidazolyl)
H H
366 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
4-(2-chloro-1-imidazolyl)
H H
367 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
4-(2-methyl-1-imidazolyl)
H H
368 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
4-(4-methyl-1-imidazolyl)
H H
369 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
4-(5-methyl-1-imidazolyl)
H H
370 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
4-(2-fluoromethyl-1-imidazolyl)
H H
371 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
4-(2-difluoromethyl-1-imidazolyl)
H H
372 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
4-(2-trifluoro-1-imidazolyl)
H H
373 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
4-(4,5-dichloro-1-imidazolyl)
H H
374 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
4-(1-imidazolyl)
3-fluoro H
375 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
4-(1-imidazolyl)
3-chloro H
376 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
4-(1-imidazolyl)
3-bromo H
377 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
4-(1-imidazolyl)
3-iodo H
378 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
4-(1-imidazolyl)
3-cyano H
379 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
4-(1-imidazolyl)
3-methyl H
380 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
4-(1-imidazolyl)
3-ethyl H
381 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
4-(1-imidazolyl)
3-isopropyl
H
382 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
4-(1-imidazolyl)
3-propyl H
383 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
4-(1-imidazolyl)
3-methoxy
H
384 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
4-(1-imidazolyl)
3-ethoxy H
385 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
4-(1-imidazolyl)
3-isopropoxy
H
386 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
4-(1-imidazolyl)
3-propoxy
H
387 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
4-(1-imidazolyl)
3-trifluoromethyl
H
388 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
4-(2-pyridyl) H H
389 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
4-(3-pyridyl) H H
390 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
4-(4-pyridyl) H H
391 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
3-fluoro H H
392 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
3-chloro H H
393 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
3-cyano H H
394 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
3-methyl H H
395 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
3-methoxy H H
396 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
3-(1-imidazolyl)
H H
397 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
3-(2-methyl-1-imidazolyl)
H H
398 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
3-(2-ethyl-1-imidazolyl)
H H
399 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
3-(2-isopropyl-1-imidazolyl)
H H
400 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
3-(2-propyl-1-imidazolyl)
H H
401 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
3-(2-phenyl-1-imidazolyl)
H H
402 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
3-(2-iodo-1-imidazolyl)
H H
403 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
3-(2-methoxy-1-imidazolyl)
H H
404 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
3-(2-methylthio-1-imidazolyl)
H H
405 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
3-(2-cyano-1-imidazolyl)
H H
406 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
3-(2-chloro-1-imidazolyl)
H H
407 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
3-(2-methyl-1-imidazolyl)
H H
408 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
3-(4-methyl-1-imidazolyl)
H H
409 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
3-(5-methyl-1-imidazolyl)
H H
410 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
3-(2-fluoromethyl-1-imidazolyl)
H H
411 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
3-(2-difluoromethyl-1-imidazolyl)
H H
412 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
3-(2-trifluoromethyl-1-imidazolyl)
H H
413 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
3-(4,5dichloro-1-imidazolyl)
H H
414 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
3-(1-imidazolyl)
4-fluoro H
415 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
3-(1-imidazolyl)
4-chloro H
416 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
3-(1-imidazolyl)
4-bromo H
417 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
3-(1-imidazolyl)
4-iodo H
418 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
3-(1-imidazolyl)
4-cyano H
419 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
3-(1-imidazolyl)
4-methyl H
420 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
3-(1-imidazolyl)
4-ethyl H
421 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
3-(1-imidazolyl)
4-isopropyl
H
422 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
3-(1-imidazolyl)
4-propyl H
423 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
3-(1-imidazolyl)
4-methoxy
H
424 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
3-(1-imidazolyl)
4-ethoxy H
425 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
3-(1-imidazolyl)
4-isopropoxy
H
426 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
3-(1-imidazolyl)
4-propoxy
H
427 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
3-(1-imidazolyl)
4-trifluoromethyl
H
428 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
3-(1-imidazolyl)
H H
429 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
3-(2-methoxy-1-imidazolyl)
H H
430 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
3-(2-methylthio-1-imidazolyl)
H H
431 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
3-(2-pyridyl) H H
432 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
3-(3-pyridyl) H H
433 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
3-(4-pyridyl) H H
434 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
3-trifluoromethyl
4-chloro H
435 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
3-methoxy 4-methoxy
H
436 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
3-(1-pyrrolyl) H H
437 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
4-(1-pyrazolyl) H H
438 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
4-(1-(1,2,4-triazolyl))
H H
439 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
4-(1-(2-pyridonyl))
H H
440 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
4-(2-imidazolyl)
H H
441 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
4-(2-pyridyl) H H
442 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
4-(3-pyridyl) H H
443 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
4-(4-pyridyl) H H
444 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
4-(1-thiazolyl) H H
445 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
4-(2-thiazolyl) H H
446 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
4-(1-oxazolyl) H H
447 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
4-(2-oxazolyl) H H
448 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
4-(1-pyrrolyl) H H
449 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
4-(1-pyridazinyl)
H H
450 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
4-(1-pyrimidinyl)
H H
451 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
2-(1-imidazolyl)
H H
452 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
2-(2-methyl-1-imidazolyl)
H H
453 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
2-(2-ethyl-1-imidazolyl)
H H
454 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
2-(2-isopropyl-1-imidazolyl)
H H
455 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
2-(2-propyl-1-imidazolyl)
H H
456 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
2-(2-phenyl-1-imidazolyl)
H H
457 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
2-(2-iodo-1-imidazolyl)
H H
458 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
2-(2-methoxy-1-imidazolyl)
H H
459 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
2-(2-methylthio-1-imidazolyl)
H H
460 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
2-2-cyano-1-imidazolyl)
H H
461 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
2-(2-chloro-1-imidazolyl)
H H
462 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
2-(2-methyl-1-imidazolyl)
H H
463 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
2-(4-methyl-1-imidazolyl)
H H
464 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
2-(5-methyl-1-imidazolyl)
H H
465 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
2-(2-fluoromethyl-1-imidazolyl)
H H
466 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
2-(2-difluoromethyl-1-imidazolyl)
H H
467 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
2-(2-trifluoromethyl-1-imidazolyl)
H H
469 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
2-(1-imidazolyl)
3-fluoro H
470 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
2-(1-imidazolyl)
3-chloro H
471 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
2-(1-imidazolyl)
3-bromo H
472 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
2-(1-imidazolyl)
3-iodo H
473 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
2-(1-imidazolyl)
3-cyano H
474 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
2-(1-imidazolyl)
3-methyl H
475 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
2-(1-imidazolyl)
3-ethyl H
476 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
2-(1-imidazolyl)
3-isopropyl
H
477 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
2-(1-imidazolyl)
3-propyl H
478 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
2-(1-imidazolyl)
3-methoxy
H
479 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
2-(1-imidazolyl)
3-ethoxy H
480 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
2-(1-imidazolyl)
3-isopropoxy
H
481 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
2-(1-imidazolyl)
3-propoxy
H
482 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
2-(1-imidazolyl)
3-trifluoromethyl
H
483 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
2-(2-pyridyl) H H
484 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
2-(3-pyridyl) H H
485 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
2-(4-pyridyl) H H
486 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
2-cyano H H
487 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
3-nitro 4-methoxy
H
488 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
3-chloro 4-chloro H
489 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
4-sulfamoyl H H
490 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
3-propoxy H H
491 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
3-chloro 4-chloro H
492 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
3-cyano 4-cyano H
493 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
2-methoxy 4-methoxy
5-methoxy
494 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 --
H H H
495 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 --
4-fluoro H H
496 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 --
4-(1-imidazolyl)
H H
497 H methyl --(CH.sub.2).sub.5 --
H H H
498 H ethyl --(CH.sub.2).sub.5 --
4-(1-imidazolyl)
H H
499 H ethyl --CH.sub.2 CH.sub.2 CH.sub.2 --
4-(1-imidazolyl)
H H
500 H ethyl H methyl
4-(1-imidazolyl)
H H
501 H ethyl methyl
methyl
4-(1-imidazolyl)
H H
502 H isopropyl
--CH.sub.2 CH.sub.2 CH.sub.2 --
4-(1-imidazolyl)
H H
503 H isoamyl
--CH.sub.2 CH.sub.2 CH.sub.2 --
4-(1-imidazolyl)
H H
504 H cyclopropyl
--CH.sub.2 CH.sub.2 CH.sub.2 --
4-(1-imidazolyl)
H H
505 methyl
methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
4-(1-imidazolyl)
H H
506 methyl
ethyl --CH.sub.2 CH.sub.2 CH.sub.2 --
4-(1-imidazolyl)
H H
507 --CH.sub.2 CH.sub.2 --
--CH.sub.2 CH.sub.2 CH.sub.2 --
4-(1-imidazolyl)
H H
508 --CH.sub.2 CH.sub.2 CH.sub.2 --
--CH.sub.2 CH.sub.2 CH.sub.2 --
4-(1-imidazolyl)
H H
509 --(CH.sub.2).sub.4 --
--CH.sub.2 CH.sub.2 CH.sub.2 --
3-(1-imidazolyl)
4-methoxy
H
510 --(CH.sub.2).sub.4 --
--CH.sub.2 CH.sub.2 CH.sub.2 --
4-(1-imidazolyl)
H H
511 --(CH.sub.2).sub.5 --
--CH.sub.2 CH.sub.2 CH.sub.2 --
4-(1-imidazolyl)
H H
512 H methyl methyl
methyl
3-(2-iodo-1-imidazolyl)
4-methoxy
H
513 H methyl methyl
methyl
3-(2-methyl-1-imidazolyl)
4-methoxy
H
514 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
4-(2-bromo-1-imidazolyl)
H H
515 H methyl methyl
methyl
3-(2-methoxy-1-imidazolyl)
4-methoxy
H
516 H methyl methyl
methyl
3-(2-iodo-1-imidazolyl)
4-ethoxy H
517 H methyl methyl
methyl
3-(2-methyl-1-imidazolyl)
4-ethoxy H
518 H methyl --CH.sub.2 CH.sub.2 CH.sub.2 --
4-(1-imidazolyl)
2-methoxy
H
__________________________________________________________________________
TABLE 2
__________________________________________________________________________
Com-
Melting NMR
Example
pound
point IR Solvent; CDCl.sub.3 [(CD.sub.3).sub.2 SO in Example
3],
No. No. (.degree.C.)
(cm.sup.-1)
.delta. value (ppm)
__________________________________________________________________________
2 208 106-108
1680
1.60(d, 3H), 3.17(3H, d), 5.11(q, 1H), 7.14-7.21(m,
2H),
8.10-8.16(m, 2H), 8.60(broad, 1H)
3 212 217-219
1685
1.37(d, 3H), 2.94(d, 3H), 4.83(q, 1H), 7.13(s, 1H),
7.78(d, 2H), 7.85(s, 1H), 7.98(d, 2H), 8.39(s, 1H),
10.51(1H, broad)DMSO-d6)
4 220 189-190
1643
1.61(s, 6H), 3.04(s, 6H), 3.12(d, 3H), 6.61(d, 2H),
7.87(d, 2H)
5 221 120-122
1660
1.62(s, 6H), 3.18(d, 3H), 7.02-7.10(m, 2H),
7.30(broad, 1H), 7.89-7.96(m, 2H)
6 222 145 1664
1.61(s, 6H), 3.17(d, 3H), 7.2-7.3(broad, 1H), 7.54(m,
2H),
7.74(m, 2H)
7 226 179 1670
1.65(s, 6H), 3.20(d, 3H), 7.25(s, 1H), 7.3-7.4(broad,
1H),
7.44(d, 2H), 7.96(1s, 1H), 8.06(d, 2H)
8 261 108.5-110
1665
1.62(s, 6H), 3.19(d, 3H), 7.21(m, 1H), 7.2-7.3(broad,
1H),
7.37(m, 1H), 7.56(m, 1H), 7.66(m, 1H)
9 262 101-101.5
1670
1.62(s, 6H), 3.19(d, 3H), 7.2-7.4(broad, 1H), 7.32(m,
1H),
7.48(m, 1H), 7.75(m, 1H), 7.85(m, 1H)
10 342 154.5-155.5
1670
1.50(m, 2H), 1.86(m, 2H), 3.11(d, 3H), 7.26(s, 1H),
7.35(s, 1H), 7.49(d, 2H), 7.98(s, 1H), 8.19(d, 2H)
11 345 113-114
1647
1.78(m, 1H), 2.05(m, 1H), 2.83(m, 2H), 2.96(m, 2H),
3.11(d, 3H), 7.41(m, 3H), 7.53(t, 2H), 7.96(d, 2H)
12 346 115-116
1660
1.80(m, 1H), 2.02(m, 1H), 2.83(m, 2H), 2.98(m, 2H),
3.11(d, 3H), 7.09(t, 2H), 7.2-7.4(broad, 1H), 8.02(m,
2H)
13 347 151.5
1648
1.81(m, 1H), 2.202(m, 1H), 2.75-2.85(m, 2H),
2.90-3.00(m, 2H), 3.11(d, 3H), 7.2-7.3(drs, 1H),
7.40(m, 2H), 7.93(m, 2H)
14 348 162-163
1648
1.81(m, 1H), 2.02(m, 1H), 2.75-2.85(m, 2H),
2.90-3.00(m, 2H), 3.11(d, 3H), 7.2-7.3(broad, 1H),
7.55(m, 2H), 7.85(m, 2H)
15 352 11.8.5-119
1672
1.82(m, 1H), 2.06(m, 1H), 2.75-2.85(m, 2H),
2.93-3.05(m, 2H), 3.12(d, 3H), 7.2-7.3(broad, 1H),
7.68(m, 2H), 8.10(m, 2H)
16 357 230 1670
1.80(m, 1H), 2.05(m, 1H), 2.41(s, 3H), 2.88(m, 2H),
3.00(m, 2H), 3.14(d, 3H), 7.02(s, 1H), 7.05(s, 1H),
7.3-7.4(broad, 1H), 7.37(d, 2H), 8.14(d, 2H)
17 358 135-135.5
1685
1.28(t, 3H), 1.80(m, 1H), 2.17(m, 1H), 2.70(q, 2H),
2.87(m, 2H), 3.00(m, 2H), 3.14(d, 3H), 6.99(s, 1H),
7.07(s, 1H), 7.35(d, 2H), 7.3-7.4(broad, 1H), 8.13(d,
2H)
18 359 193-195
1675
1.26(d, 6H), 1.76-1.91(m, 1H), 2.01-2.18(m, 1H),
2.80-3.08(m, 5H), 3.15(d, 3H), 6.94(d, 1H), 7.08(d,
1H),
7.34(broad, 1H), 7.35(d, 2H), 8.13(d, 2H)
19 360 162-164
1675
0.90(t, 3H), 1.65-1.90(m, 4H), 2.00-2.15(m, 1H)
2.64(t, 2H), 2.80-2.92(m, 2H), 2.97-3.08(m, 2H),
3.15(d, 3H), 6.98(d, 1H), 7.08(d, 1H), 7.35(d, 2H),
7.42(broad, 1H), 8.12(d, 2H)
20 361 amorphous
1670
1.76-1.90(m, 1H), 2.00-2.16(m, 1H), 2.80-2.89(m, 2H),
2.93-3.08(m, 2H), 3.13(d, 3H), 7.17(d, 1H),
7.24-7.39(m, 9H), 8.01(d, 2H)
21 362 163-165
1670
1.76-1.88(m, 1H), 2.01-2.14(m, 1H), 2.80-2.92(m, 2H),
(decom- 2.97-3.08(m, 2H), 3.15(d, 3H), 7.20(d, 1H), 7.23(d,
1H),
position) 7.34(broad, 1H), 7.44(d, 2H), 8.14(d, 2H)
22 368 180 1660
1.80(m, 1H), 2.05(m, 1H), 2.29(s, 3H), 2.80(m, 2H),
2.98(m, 2H), 3.12(d, 3H), 7.06(s, 1H), 7.2-7.4(broad,
1H),
7.40(d, 2H), 7.65(s, 1H), 8.12(d, 2H)
23 369 220-220.5
1685
1.80(m, 1H), 2.00(m, 1H), 2.22(s, 3H), 2.86(m, 2H),
3.00(m, 2H), 3.14(d, 3H), 6.93(s, 1H), 7.36(d, 2H),
7.4-7.5(broad, 1H), 7.58(s, 1H), 8.16(d, 2H)
24 373 184-186
1665
1.76-1.92(m, 1H), 2.00-2.18(m, 1H), 2.79-2.91(m, 2H),
2.96-3.08(m, 2H), 3.14(d, 3H), 7.33(broad, 1H),
7.45(d, 2H), 7.57(s, 1H), 8.18(d, 2H)
25 374 162-164
1670
1.83(m, 1H), 2.07(m, 1H), 2.87(m, 2H), 2.99(m, 2H),
3.13(d, 3H), 7.25(s, 1H), 7.32(s, 1H), 7.7-7.9(broad,
1H),
7.47(t, 1H), 7.92(s, 1H), 7.95(m, 2H)
26 375 173 1670
1.83(m, 1H), 2.05(m, 1H), 2.80-2.90(m, 2H),
2.95-3.02(m, 2H), 3.12(d, 3H), 7.19(m, 1H), 7.22(m,
1H),
7.2-7.3(broad, 1H), 7.38(d, 1H), 7.75(s, 1H), 8.02(m,
1H),
8.23(d, 1H)
27 378 156 2250,
1.85(m, 1H, 2.05(m, 1H), 2.80-2.90(m, 2H),
1680
2.95-3.03(m, 2H), 3.12(d, 3H), 7.29(s, 1H), 7.41(m,
1H),
7.5-7.6(broad, 1H), 7.50-7.54(d, 1H), 7.94(s, 1H),
8.38-8.42(m, 1H), 8.50(m, 1H)
28 392 119.5-120
1663
1.81(m, 1H), 2.02(m, 1H), 2.75-2.85(m, 2H),
2.92-3.05(m, 2H), 3.11(d, 3H), 7.2-7.3(broad, 1H),
7.35(t, 1H), 7.50(m, 1H), 7.85(d, 1H), 7.97(d, 1H)
29 396 198 1671
1.83(m, 1H), 2.05(m, 1H), 2.80-2.90(m, 2H),
2.95(m, 2H), 3.13(d, 3H), 7.24(s, 1H), 7.2-7.3(broad,
1H),
7.34(s, 1H), 7.50-7.57(m, 2H), 7.80-7.93(m, 2H),
8.14(s, 1H)
30 404 147.5-149.5
1670
1.83(m, 1H), 2.07(m, 1H), 2.62(s, 3H), 2.90(m, 2H),
2.99(m, 2H), 3.13(d, 3H), 7.13(s, 1H), 7.18(s, 1H),
7.25-7.4(broad, 1H), 7.5-7.6(m, 2H), 8.02-8.06(m, 2H)
31 434 137 1666
1.82(m, 1H), 2.04(m, 1H), 2.75-2.85(m, 2H),
2.93-3.03(m, 2H), 3.11(d, 3H), 7.2-7.3(broad, 1H),
7.55(m, 1H), 8.12(m, 1H), 8.38(m, 1H)
32 437 177-179
1655
1.80(m, 1H), 2.06(m, 1H). 2.85(m, 2H), 3.01(m, 2H),
3.12(d, 3H), 6.51(dd, 1H), 7.2-7.4(broad, 1H),
7.75(d, 1H), 7.77(d, 2H), 7.98(d, 1H), 8.09(d, 2H)
33 438 200-200.5
1665
1.80(m, 1H), 2.06(m, 1H), 2.87(m, 2H), 3.00(m, 2H),
3.12(d, 3H), 7.2-7.3(broad, 1H), 7.79(d, 2H), 8.13(s,
1H),
8.16(d, 2H), 8.63(s, 1H)
34 439 209-209.5
1670
1.80(m, 1H), 2.05(m, 1H), 2.83(m, 1H). 2.98(m, 1H),
3.12(d, 3H), 6.27(t, 1H), 6.67(d, 1H), 7.29(m, 1H),
7.2-7.3(broad, 1H), 7.40(m, 1H), 7.46(d, 2H), 8.13(d,
2H)
35 495 110-111
1662
1.58(m, 2H), 1.77(m, 2H), 3.11(d, 3H), 7.05(m, 2H),
7.1-7.2(broad, 1H), 8.04(m, 2H)
36 496 175-176
1673
1.59(m, 2H), 1.79(m, 2H), 2.4-2.6(m, 4H), 3.13(d,
3H),
7.23(s, 1H), 7.33(s, 1H), 7.44(d, 2H), 7.93(s, 1H),
8.15(d, 2H)
37 500 206.5-207.5
1680
1.27(t, 3H), 1.61(d, 3H), 3.68(m, 2H), 5.15(q, 1H),
7.2-7.3(broad, 1H), 7.26(s, 1H), 7.53(d, 2H), 7.99(s,
1H),
8.24(d, 2H)
38 514 205-207
1678
1.76-1.90(m, 1H), 2.01-2.15(m, 1H), 2.80-2.91(m, 2H),
2.96-3.08(m, 2H), 3.14(d, 3H), 7.16(s, 2H), 7.34(d,
1H),
7.46(dd, 2H), 8.14(dd, 2H)
39 518 168 1658
1.75(m, 1H), 2.04(m, 1H), 2.63(m, 2H), 2.90(m, 2H),
3.17(d, 3H), 3.88(s, 3H), 6.89(d, 1H), 7.04(dd, 1H),
7.23(d, 1H), 7.31(d, 1H), 7.60(broad, 1H), 7.78(d,
__________________________________________________________________________
1H)
TABLE 3
__________________________________________________________________________
Com-
Melting
Example
pound
point IR NMR
No. No. (.degree.C.)
(cm.sup.-1)
Solvent; CDCl.sub.3, .delta. value (ppm)
__________________________________________________________________________
41 218 99-101
1670
1.61(s, 6H), 2.38(s, 3H), 3.16(d, 3H), 7.18(d, 2H),
7.29(broad, 1H), 7.78(d, 2H)
42 219 133-135
1650
1.62(s, 6H), 3.16(d, 3H), 3.84(s, 3H), 6.86(d, 2H),
7.31(broad, 1H), 7.90(d, 2H)
43 224 oil 1677
1.62(s, 6H), 3.21(d, 3H), 7.54(broad, 1H), 7.69(d,
2H),
7.95(d, 2H)
44 263 101-102
1670
1.62(s, 6H), 2.36(s, 3H), 3.17(d, 3H), 7.2-7.4(broad,
3H),
7.6-7.7(m, 2H)
45 264 73.5-74.5
1675
1.63(s, 3H), 3.17(d, 3H), 3.80(s, 3H), 7.06(dd, 1H),
7.2-7.3(broad, 1H), 7.31(d, 1H), 7.43-7.48(m, 2H)
46 265 138 1680
1.66(s, 3H), 3.20(d, 3H), 7.21(s, 1H), 7.30(s, 1H),
7.52(m, 2H), 7.6-7.9(broad, 1H), 7.88(m, 2H),
8.00(s, 1H)
47 302 152.5-163.5
1680
1.39(s, 3H), 3.16(d, 3H), 7.07(s, 1H), 7.08(s, 1H),
7.32(d, 1H), 7l.42(m, 2H), 7.50(m, 1H), 7.53(s, 1H),
7.7-7.9(broad, 1H)
48 338 183-184
1665
0.75(t, 6H), 2.1-2.3(m, 4H), 3.22(d, 3H), 7.23(s,
1H),
7.32(s, 1H), 7.42(d, 2H), 7.93(s, 1H), 8.08(d, 2H)
49 351 150-151
1634
1.80(m, 1H), 2.05(m, 1H), 2.85(m, 2H), 2.95(m, 2H),
3.10(d, 3H), 3.85(s, 3H), 6.89(d, 2H), 7.40(broad,
1H),
7.95(d, 2H)
50 423 174-175
1663
1.81(m, 1H), 2.04(m, 1H), 2.86(m, 1H), 2.97(m, 2H),
3.12(d, 3H), 3.93(s, 3H), 7.06(d, 1H), 7.18(s, 1H),
7.23(s, 1H), 7.2-7.3(broad, 1H), 7.83(s, 1H), 8.03(s,
1H),
8.05(dd, 1H)
51 435 165-167
1632
1.80(m, 1H), 2.05(m, 1H), 2.86(m, 2H), 2.98(m, 2H),
3.10(d, 3H), 3.90(s, 3H), 3.93(m, 3H), 6.86(d, 1H),
7.31(broad, 1H), 7.55(d, 1H), 7.64(q, 1H)
52 436 123.5-124.5
1665
1.82(m, 1H), 2.06(m, 1H), 2.85(m, 2H), 3.05(m, 2H),
3.26(d, 3H), 6.37(m, 2H), 7.14(m, 2H), 7.2-7.3(broad),
1H),
7.47(t, 1H), 7.56(m, 1H), 7.82(m, 1H), 8.10(m, 1H)
53 497 124-126
1665
1.16-1.32(m, 3H), 1.52-1.74(m, 3H), 1.94-2.12(m, 2H),
2.40-3.16(m, 2H), 3.16(d, 3H), 7.35-7.53(m, 4H),
7.80(d, 2H)
54 498 189-191
1665
1.18(t, 3H), 1.2-1.3(broad, 4H), 1.5-1.65(broad, 2H),
1.9-2.1(m, 2H), 2.2-2.6(m, 2H), 3.70(m, 2H), 7.24(s,
1H),
7.33(s, 1H), 7.43(d, 2H), 7.93(s, 1H), 8.00(d, 2H)
55 503 137-139
1675
0.84(d, 6H), 1.37-1.53(m, 3H), 1.75-1.87(m, 1H),
2.00-2.13(m, 1H), 2.77-2.89(m, 2H), 2.94-3.05(m, 2H),
3.57-3.64(m, 2H), 7.12(broad, 1H), 7.24(s, 1H),
7.33(s, 1H),
7.47(d, 2H), 7.94(s, 1H), 8.15(d, 2H)
56 505 amorphous
1665
1.88-2.12(m, 2H), 2.60-3.40(m, 4H), 2.99(s, 3H),
3.36(m, 3H), 7.23(s, 1H), 7.32(s, 1H), 7.43(d, 2H),
7.93(s, 1H), 8.30(d, 2H)
57 509 135-135.5
1667
1.75-2.0(m, 5H), 2.0-2.15(m, 1H), 2.6-3.2(broad, 4H),
3.23-3.3(broad, 2H), 3.80(t, 2H), 3.92(s, 3H),
7.05(d, 1H), 7.18(s, 1H), 7.29(s, 1H), 7.88(s, 1H),
7.19(d, 1H), 8.21(dd, 1H)
__________________________________________________________________________
TABLE 4
__________________________________________________________________________
Com-
Melting
Example
pound
point IR NMR
No. No. (.degree.C.)
(cm.sup.-1)
Solvent; CDCl.sub.3, .delta. value (ppm)
__________________________________________________________________________
61 270 149-151
1689
1.67(s, 6H), 3.22(d, 3H), 7.20(m, 2H), 7.50-7.65(m,
3H),
7.84(m, 1H), 8.01(m, 1H)
62 275 164-165
1682
1.65(s, 6H), 2.38(s, 3H), 3.20(d, 3H), 7.02(dd, 2H),
7.30-7.55(m, 3H), 7.82(m, 1H), 7.93(m, 1H)
63 291 162 1672
1.64(s, 6H), 3.18(d, 3H), 3.92(s, 3H), 7.03(d, 1H),
7.18(d, 1H), 7.19(s, 1H), 7.35(broad, 1H), 7.79(s,
1H),
7.95(s, 1H), 8.00(dd, 1H)
64 292 amorphous
1676
1.43(t, 3H), 1.66(s, 6H), 3.19(d, 3H), 4.16(q, 2H),
7.01(d, 1H), 7.10(s, 1H), 7.21(s, 1H), 7.77(s, 1H),
7.94(d, 1H), 8.01(dd, 1H), 8.66(broad, 1H)
65 305 145-146
1693
1.27(d, 6H), 1.46(s, 6H), 2.78(m, 1H), 3.18(d, 3H),
6.79(d, 1H), 7.03(d, 1H), 7.28-7.33(m, 1H),
7.43-7.58(m, 3H), 7.80(s, 1H)
66 337 192-193
1678
1.63(s, 6H), 3.14(d, 3H), 3.82(s, 6H), 3.90(s, 3H),
7.10(broad, 1H), 7.25(s, 2H)
67 512 amorphous
1676
1.65(s, 6H), 3.19(d, 3H), 3.66(s, 3H), 7.03(d, 1H),
7.09(d, 1H), 7.19(d, 1H), 7.36(broad, 1H), 7.82(d,
1H),
8.12(dd, 1H)
68 513 206 1676
1.64(s, 6H), 2.19(s, 3H), 3.18(d, 3H), 3.86(s, 3H),
6.88(s, 1H), 7.01(d, 1H), 7.02(s, 1H), 7.51(broad,
1H),
7.81(d, 1H), 8.07(dd, 1H)
69 515 173.5-174
1680
1.64(s, 6H), 3.16(d, 3H), 3.25(s, 3H), 3.85(s, 3H),
4.36(s, 2H), 6.99(s, 1H), 7.01(d, 1H), 7.35(broad,
1H),
7.90(d, 1H), 8.07(dd, 1H)
70 516 165-168
1684
1.35(t, 3H), 165(s, 6H), 3.19(d, 3H), 4.12(q, 2H),
(decom- 7.00(d, 1H), 7.08(d, 1H), 7.18(d, 1H), 7.41(broad,
1H),
position) 7.81(d, 1H), 8.09(dd, 1H)
71 517 178-179
1676
1.34(t, 3H), 1.64(s, 6H), 2.21(s, 3H), 3.18(d, 3H),
4.11(q, 2H), 6.87(s, 1H), 6.99(d, 1H), 7.01(s, 1H),
7.47(broad, 1H), 7.80(d, 1H), 8.03(dd, 1H)
72 6 185-187
1671
1.84(m, 1H), 2.10(m, 1H), 2.9-3.1(m, 4H),
6.85(broad, 1H), 7.24(s, 1H), 7.34(s, 1H),
7.34(broad, 1H), 7.47(d, 2H), 7.95(s, 1H), 8.14(d,
__________________________________________________________________________
2H)
TABLE 5
______________________________________
##STR13## Compound A
Compound No. Rat aorta
in Table 1 IC30 20 mMK (.mu.M)
______________________________________
224 5.0
226 13.0
265 0.62
356 2.1
357 0.18
Compound A 13.6
______________________________________
TABLE 6
______________________________________
Mean blood pressure (mm Hg)
Compound No.
Dose Value prior to
Blood pressure
in Table 1 (mg/kg) dosing decrease
______________________________________
224 10 177.5 38.8
226 10 177.3 35.9
265 3 163.1 76.5
302 10 176.1 51.9
342 10 167.3 31.2
356 10 172.0 58.9
357 10 158.4 78.4
Compound A 10 180.3 14.1
______________________________________